Benzyl Bromide → (1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate

HRID 2179726ノート

反応式

HRID 2179726 の反応式
[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

生成物 1

HCID 58111012(1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate収率 61.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (6.0 g, 35.29 mmol) in DMF (20 ml) at 0° C., Cs2CO3 (13.8 g, 42.34 mmol) followed by BnBr (5.06 ml, 42.34 mmol) were added slowly portion wise. The reaction was stirred at room temperature for about 2 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc (100 ml) and washed with water (50 ml), brine (50 ml) and dried with Na2SO4. The solvent was evaporated and purified by silica gel column (60-120, elution 4% EtOAc in hexane) to afford title compound as a pale yellow syrup. Wt: 5.6 g; Yield: 61.5%; 1H NMR (300 MHZ, CDCl3): δ 7.42-7.31 (m, 5H), 5.13 (s, 2H), 2.93-2.81 (m, 2H), 2.68 (q, 1H, J=10.5 Hz,), 2.05 (s, 3H), 1.97-1.88 (m, 1H), 1.43 (s, 3H), 0.87 (s, 3H); Mass: [M+1]+ 261 (20%), [M+Na]+ 283 (87%); IR (KBr, cm−1): 2889, 1732, 1708, 1498, 1456, 1329, 1279, 1183, 1027, 954, 752, 698.

後処理

  1. customat 0° C.
  2. additionwere added slowly portion wise
  3. customAfter completion of the reaction (monitored by TLC)
  4. washwashed with water (50 ml), brine (50 ml)
  5. dry with materialdried with Na2SO4
  6. customThe solvent was evaporated
  7. custompurified by silica gel column (60-120, elution 4% EtOAc in hexane)

出典と根拠

ORDレコード
ord-1abef5ae2eba443da0c6ff77ab884581
出典データセット
uspto-grants-2015_06
特許番号
US09067966B2

反応ノート

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